So here's the math on mine: period is 3 months and you buy them at 10% off. You can sell immediately. So you money is tied up for 1.5 months on average. (Your first paycheck is tied up for 3 months, your middle paycheck is tied up for 1.5 months, and you last paycheck is tied up for no time). Buying for 10% off and selling it immediately gives you 11% gains (100%/90% = 111%). But this is over 1.5 months. The APY is 11%/(1.5/12), or .11*8 = 88%. Now, you will have to pay taxes on that 88% gain. If you are in a 25% tax bracket, you will take home 66% gains. Now, what you say is true: If you wait a year, you will pay long term capital gains tax instead of your marginal tax rate, but I sell immediately to avoid the risk. Stock, especially of one company, is volatile. I think the 8% loss overall (~10% (25% marginal - 15% LTCG) of 88%) is a small enough hit for me to lock in my gains. But that's me. Do what makes sense for your own risk needs.

The longer you stay in your place, the better a deal it is. Plug your situation in here to find out http://www.nytimes.com/interactive/2014/upshot/buy-rent-calculator.html. But yes, this is not a pure financial decision. Also know that is REALLY REALLY decreases your diversification as well. Instead of owning a small portion on many stocks, or a small portion of many homes, you own ALL of ONE. That changes the risk equation a good bit. Just be aware of it. But if you decide buying a place is the best overall decision, go for it!

While you are building wealth, Stock market index funds are a fantastic way to go. Add more bonds the closer you get to retirement. Actually, don't take it from me. Take it from Warren Buffet, the 2rd richest man in the world, about what he wants his wife to do when he is gone. Give those links and the sidebar a read, and let me know if you have any more questions.

First, GET SOME OF THAT ESPP!!! (if the deal is as good as it was for my company).

I ran the numbers on my company (Microsoft), and the APY is something like 88% pre tax. There's a reason they put a limit on how much you can contribute. It's because it's an insanely good deal. Now my company lets me sell immediately, so there's no risk. And the discount alone is enough to generate 88%. Again, I always sell immediately. If you must hold for some period of time, it might not be quite as good of a deal, but run the numbers yourself. It starts out pretty sweet.

By the way, as someone who lives in Redmond, I ran some numbers on "Buying outright in cash" and "renting" (my rent number is 14,400/yr) because I had considered buying. The break even point was ~150k. This number will probably be slightly higher for 15K/yr, but not by much. I would say do not buy a condo at 190K "to decrease the cost of living". Overall, just in interest payments, HOA fees, property taxes and oppurtunity cost on the money you put down, you will lose money. And all of that assumes you have no repairs that are needed (although they are often less for condos than for homes).

Now that's not to say you shouldn't buy. But you should buy because you want to own something, not as a financial decision.

Also, I'll just give my 2 cents on your real estate plans. I personally don't think their worth it. Especially in Seattle, from what I see, it's a renter's market, not a buyer's market. There's a lot of risk in one property (or a few properties). And there is enough to go wrong that I'd at least take a long hard look before making the leap. Not to say it's a bad idea. I just don't think that it's quite as lucrative as many people (even some in the FI community) make it sound.

But that's just me. Can you tell I don't have a ton of faith investing in real estate? I'll stick with stocks. But to each their own. For example, for someone that is really handy with repairs themselves, real estate might be good, because you can subsidize the costs with your own labor.

Everyone has different priorities, and why should one person tell another what their priorities should be?

At the end of the day, this place is about trading free time for utility. That's what all work is. I could stop working tomorrow and be homeless. I'd have tons of free time and virtually zero spending. But my free time is not THAT valuable to me.

At the other extreme, I could live on exactly my income and spend everything I make. I could buy that million dollar house or that ferrari, but that spending level would mean I could never retire.

In between, there are trade offs for each of us. For example, I have never gotten excited with fancy cars. I'm more than happy to drive one thats 10 years old (but reliable) that cost me a few thousand cash. Other people love their cars, and all the free time in the world would not be worth not having the car of their dreams. It's fine to spend on that.

For me, though, it's airplanes. I have dreamed of flying since I was a kid. Last year I spent 12K on getting my pilots license, and I intend to continue to spend some money flying for fun. An ideal retirement for me would be traveling the country in my small plane, and it is well worth it for me to add a few years to my career to have the freedom of hobby in retirement AND until then.

By the numbers, buying a house is a pretty terrible INVESTMENT. The answer to "should I buy this house to improve my path to FI" is almost always NO. However, the question to "should I buy this house" is very different. You gain (depending on the person, a different amount) pleasure in life, not financial gain, from owning a house. Is that financial cost worth the increase in pleasure? Maybe...that is different for each person.

The point of this place is to show the true cost in terms of free time our consumerist choices have. Buying your fancy car or house or airplane will mean you have to work an extra X years at your job. To some people, that's terrible; to others, it's fine. Who am I to tell you what you can and can't prefer?

This is where I can disagree with MMM. He values free time more than anything in the world. His wife didn't. BUT, she valued spending 100% of her time with her son, and so the value of her free time increased when she had a baby. Now when people don't realize that their lifestyle is worth 30 years of working, and if only they knew the facts of how much that car was costing them, maybe then it's ok to get up in their face to show them the facts.

But when someone knows the tradeoffs, and chooses one over the other because of differing priorities, at that point, it's time to leave them to their choices.

The best source for minimizing risk is to diversify. Partly in things like bonds. Partly in real estate. Partly in reducing debt. Partly in other things. So, yes. Paying off your house (slightly less slowly) is a decent diversification strategy.

Woah woah, no need to get angry. Of course I know what dividends are. (And I don't believe I ever said I didn't know what dividends are. I said I don't know exactly the terms of his trust. I can very much believe that someone can be told they have a trust that should be worth $X in Y years, and seem to think that it means they have $X today that they can't access right away).

I was trying to convey (but did poorly) that I don't know the details of his trust. Was 560K it's current value or it's projected value at the time he could access it? What was it invested in?

And it clearly matters, because the number I gave him assumed index fund level returns of 7%, but it appears he is invested in Tbills which only give just about 2%.

The average american family income is just under 52K (according to google). Assuming you are talking about $5M american dollars and not AUS dollars (which doing the current conversion, would give you 3.8M. henceforth, all calculation in parentheses assume you are talking about 5M AUS dollars.) should give you 200K/yr (152K/yr). Meaning you are making 4 (3) times as much as the average american family. That should be plenty.

If you are asking about housing prices, that's the biggest difference in different areas of the country. Houses can be anywhere from sub 100K, to 1-2M in the most expensive areas. Health care is a tricky subject, as the legislation is new, and how it will change in the next 5-50 years is anyone's guess, but in the US, you fund your own healthcare until Medicare (65). It's often covered by your employer, but for early retirees, you gotta get your own. But it can be had for a few hundred a month.

As for college, it also varies widely. You can get away with paying no more than 10K/child for 4 years, or as much as 150K/child for 4 years. I wouldn't expect it to be much more than that, and with 5M, it's a drop in the bucket.

Honestly, though I have no idea what lifestyle you expect, I want to ask...is 5M too much? My personal number, in a higher than average cost of living area (but not the highest): Seattle, is 1.8M and sometimes I wonder if that's too high.

What lifestyle level to you expect to have? 200K/yr puts you in the 91st percentile for all married earners in the US. For a relatively frugal life (let's say 50th percentile, but let's be honest, less than half of americans are frugal), you might only need 43K/yr or 1.1M total.

It really doesn't matter what you make. It only matters what you spend.

Also, look up the Roth Conversion Ladder. It's a way to get at the money in 401Ks or IRAs before you turn 59.5. In a nutshell, you immediately convert the 401K into a Traditional IRA (this usually requires you to not be employed at your current position). Then, every year, you do a Roth IRA conversion. You take just enough money to live on for one year out of your Traditional IRA and put it in your Roth IRA. Note, you pay taxes on this conversion, so make sure you convert enough. Then 5 years later, you can withdraw the contributions (but not the gains) on that conversion.

So year, you have to wait 5 years to access it, but if you have 5 years expenses saved up elsewhere, its doable.

Also (I don't like this other one as much), look at SEPP. It's another way to get some of that money out without penalty before 59.5.

Or you could continue working. Up to you. Just want to make sure you know all the options.

My personal retirement number is somewhere between 1.8M - 2M. And at 1M - 1.5M, I might strongly consider doing only part time or freelancing.

Do you want to live in a house you own in retirement, or rent in retirement?

What is your FI number? How much do you want before you call it quits? What is your current spending per year?

If this was me, this is what I would do:

If you plan to rent in retirement, selling now is a good idea. You can extract that value from your home and put it to work. Yay! Better to do it now than later.

If you plan to own in retirement, I doubt you'd come out much ahead with the sell, then buy scheme you have here, but run the numbers yourself to be sure.

How far are you from retirement? You didn't say what your number was, so I have no idea. But I'd look at how many years selling your home would save off your working career. If it is 1 year, you might want to just keep the house. If it's close to 20%, you might consider selling.

If you want 50K/yr, (and assuming you'll use a 4% SWR) you'll need 1.25M to retire. Adjust this up using the 4% rule if you expect your spending will increase with kids.

Now, in 10 years, assuming 7% interest rate, that 560K will be worth 1.125M. (I assume the trust money is invested and earning interest and that it is 560K today, but I don't really know how trust funds work).

But wait! You won't have access to that 1.125M in 10 years. Only 2/3rds of that, so 750K. That's not enough to retire off.

So it sounds like you have two options.

Put off retirement until age 40 when you can access the whole thing. Additionally, you will need to save 125K yourself in the next 14 years. That's about 450 bucks a month.

Retire at age 36. Use the last 1/3rd as a safety or to fund expensive things like kid's college funds at age 40+. To do this, you'll need to save 750K in 10 years yourself. That's about 4,350/mo. That sounds like a lot, given that your yearly take home is close to that. You'd have to make a lot of side money to make that happen.

All of this assumes that you do not touch the 12K in dividends each year. If you take the dividends, you will not have 1.125M in 15 years (or 750K in 10), you will have 560K (or 373K in 10) which will not be enough to retire on. If you must take them, invest them yourself. DO NOT SPEND THE 12K/yr!!!

You say this past year you spent 47,576 and that your budget is 40,000. Where did the other 7,576 go? Is that your estimated spending drop in retirement? If you don't mind sharing, what in the budget changed?

Meh. In really good years, it will get you $200/yr. Something, but not world changing. Depends on how you use it (investment vehicle, or actual checking account for medical expenses) and your tolerance for risk. Either would be fine. (I have about 800 in mine that is more or less in a savings account, but I actively use it for medical expenses).

-Do I need to expand my portfolio to stocks or other riskier options?

You never "need" to go with riskier options. But it might not hurt. Depends on how far from FIRE you think you are. 5 years? You are probably fine. But I doubt you are 5 years. You could probably do better with more risk, but it isn't required. You don't mention what your 401K is in, but you say the Roth is in a target date fund. I'll assume the 401K is also. It is probably more optimal to put them both in a full Vanguard index fund if you can and your 401K plan has that option (or some index fund if not). This is more risky, but you have plenty of time, so you can take that risk on. I wouldn't tempt any riskier than a agood solid Vanguard index fund, but that's just me. Everyone has their own tolerances for risk.

-Is there anything I should do with my accounts prior to leaving a company, like maxing out 401k contributions? I already know I'll miss the employer match.

Look into front loading your 401K. If you would get matched on 6K that you put in, instead of putting in $500/mo, you could put in 6K as fast as you can hoping to get company match for 6K before you bolt. Know that some companies won't match at the same rate. For example, I have already contributed something like 11K to my 401K this year, and I'm due to hit my 18K limit in Mach or April. My company matches up to 3K/yr (for my salary), but so far has only put in about 350/mo. But they will continue putting in 350/mo for the rest of the year. Just look into the match program for the details, but if they will front load with you, that is free money that you can get before leaving.

-Finding a new job, or role within my current company.

If your company has offices where you'd like to move, your first step is talking to someone at your current company to see if transfering there is an option. (It sounds like you like the job, but not the city? If there is something about the company you don't like, ignore the previous statement, but in general, you're best source of a new job is through your current job).

MOST IMPORTANT: DO NOT MOVE TO A NEW PLACE WITHOUT ANOTHER JOB LINED UP.

I don't care how good of a tech hub it is. Even a move yourself could put you back a significant portion of your FI progress. Not to mention what if it takes a few months to find a job. Or longer.

And if youi get a job before moving, you might get some/all of your moving costs paid for/reimnbursed.

Seriously, make sure you have a job to go to before you leave. It's the path to FI. Even if it means staying in your job a few extra months.

Look at it this way: If they really are as easy to find as you say, you'll find one in no time and move out in no time. If it takes you a while now and you are stuck at your job, imagine how bad it would be without a stream of income.

-I'm going to need a new car. Lease/buy? Do I dabble in the electric market or lease for a while as infrastructure develops.

Buy, cheap, used. Until you have a job, you are poor. You have 100K, much of which you can't access. That means you male 4-8K /yr. That's low. Buy a cheap used car at least until you have another paycheck rolling in. (Or better yet, always buy cheap used cars, but everyone has their own priorities, so I won't preach mine).

-Switching roles or moving long distances while staying within the same company.
-How you approached management with the above kind of decisions would be awesome too!

A lot of this is a case by case basis. Depends on the relationship you have with your boss, HR, and your company in general. It must be approached in the right way. Some bosses, just asking might get you fired. Others, it will land you the perfect role in the perfect fit. It all depends on the people around you.

Good luck. No amount of money is worth a job or city you hate, and it sounds like moving is the right choice for you. It also sounds like you have MOST of your ducks in a row and you've done your research. Go ahead and take the leap, just make sure you have something lined up out there.